Organophosphines

Abstract

Organophosphines of the formula (R) a P(H) 3−a ( where R is C1-C20 alkyl, alkenyl, alkaryl or styryl and a is 1, 2, or 3) are produced by (i) reacting a tris(hydroxyorgano)phosphine (THP) with an organic halogen containing compound; (ii) reacting the product of (i) with a base; (iii) removing aldehydes from the product of (ii) and adding an organic phase, followed by distillation or phase-separation to obtain the desired product.

What is claimed is:  
     
       1. A method for the production of a primary, secondary or tertiary phosphine having the formula (R) a P(H) 3−a  where R is an organic group and a is 1, 2 or 3, wherein said method comprises the following stages: 
       (i) reacting a tris(hydroxyorgano)phosphine (THP) with an organic halogen-containing compound, of formula R(X) n  where:  
       R is selected from the group consisting of C 1  to C 20  alkyl, alkenyl, alkynyl, alkaryl and styryl;  
       X represents a halogen atom;  
       n is a whole number of from 1 to 4 and said R includes at least one aliphatic carbon atom adjacent each said halogen atom;  
        said stage (i) being carried out at a temperature of less than about 90° C. and at ambient pressure and in the presence of a solvent;  
       (ii) reacting the product of stage (i) with a base;  
       (iii) thereafter adding, to the resulting product of stage (ii), sufficient of an acid to maintain a pH of 6 to 8, removing aldehydes from said product of stage (ii) and adding to said product a material to form a discrete organic phase, followed by distilling or phase-separation to obtain said primary, secondary or tertiary phosphine.  
     
     
       2. The method of  claim 1 , wherein each hydroxy group present in said THP is attached to the carbon atom which is joined to the phosphorus atom of said THP. 
     
     
       3. The method of  claim 1 , wherein said organic halogen-containing compound is present in said reaction in a stoichiometric excess amount of up to 10:1 by equivalent weight, relative to said THP. 
     
     
       4. The method of  claim 1 , wherein said organic halogen-containing compound is present in said reaction in an amount of 2:1 to 3:1 by equivalent weight, relative to said THP. 
     
     
       5. The method of  claim 1 , wherein said stage (i) is carried out in an inert atmosphere. 
     
     
       6. The method of  claim 5 , wherein said inert atmosphere consists essentially of a gas selected from the group consisting of nitrogen and argon. 
     
     
       7. The method of  claim 1 , wherein said solvent is selected from the group consisting of water and water/alcohol mixtures, said solvent being present in an amount sufficient to solubilise said organic halogen containing compound. 
     
     
       8. The method of  claim 1 , wherein said group R contains from 2 to 8 carbon atoms. 
     
     
       9. The method of  claim 1 , wherein said atom X is selected from the group consisting of chlorine, bromine and iodine. 
     
     
       10. The method of  claim 1 , wherein said organic halogen-containing compound is selected from the group consisting of ethyl bromide, butyl bromide, 1,2-dibromo-ethane and 1,3-dibromo-propane. 
     
     
       11. The method of  claim 1 , wherein said group R contains at least one ether-linkage or at least one amino-linkage. 
     
     
       12. The method of  claim 1 , wherein, in said stage (iii), said removal of aldehydes is achieved by adding sodium sulphite. 
     
     
       13. The method of  claim 1 , wherein, in said stage (iii) said acid is selected from the group consisting of hydrochloric acid, phosphoric acid and acetic acid. 
     
     
       14. The method of  claim 1 , wherein, in said stage (iii), said material to form a discrete organic phase consists essentially of a substance selected from the group consisting of mineral oils and petroleum ethers. 
     
     
       15. The method of  claim 1 , wherein said THP is first obtained by reacting a tetrakis(hydroxyalkyl)phosphonium salt with a base. 
     
     
       16. A method of  claim 12 , wherein said tetrakis(hydroxymethyl phosphonium salt is selected from the group consisting of tetrakis(hydroxymethyl)phosphonium chloride and tetrakis(hydroxymethyl)phosphonium sulphate.